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Theo Chukka Boot

Theo Chukka Boot

Men's Thomas & Vine Theo Chukka Boot - Brown - Casual boots The Theo chukka boot from Thomas & Vine is a happy medium between casual and formal. Boasting a low-cut profile, this boot showcases 12mm Tru Comfort Foam insole that delivers cushioned... more

$49.99

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Keith Chukka Boot

Keith Chukka Boot

Men's Drew Keith Chukka Boot - Brown - Casual boots Stay stylish without sacrificing comfort with the Keith chukka boot from Drew. This ankle boot features a Gel System footbed and sole to absorb impact! Leather upper. Lace-up closure. Padded collar.... more

$193.99

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Best Seller
Heston Chukka Boot

Heston Chukka Boot

Men's Steve Madden Heston Chukka Boot - Brown - Casual boots Leather upper. Lace-up closure. Breathable mesh lining. Rubber sole. more

$89.99

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Medium DDB0248-105-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Medium DDB0248-105-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Medium DDB0248-105-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

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Vance Co. Shoes Barett Knit Chukka Boot - Grey - 12

Vance Co. Shoes Barett Knit Chukka Boot - Grey - 12

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Duck and Cover Mens Glutinosa Leather Chukka Boots - Black - Black - UK 9 / US 10

Duck and Cover Mens Glutinosa Leather Chukka Boots - Black - Black - UK 9 / US 10

Men's chukka boot with shoe lace fastener. Contrast metallic eyelets and contrast mesh inner sock lining. more

$106.99 $61.70

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Vance Co. Shoes Barett Knit Chukka Boot - Grey - 13

Vance Co. Shoes Barett Knit Chukka Boot - Grey - 13

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Nunn Bush Circuit DC Plain Toe Chukka Boot - Mens 12 Brown Boot Medium

Nunn Bush Circuit DC Plain Toe Chukka Boot - Mens 12 Brown Boot Medium

*Casual boot from Nunn Bush *Mixed-material upper *Lace-up front closure *Breathable mesh linings *Fully cushioned Comfort Gel footbed *Two-toned outsole more

$84.95

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Nunn Bush Circuit DC Plain Toe Chukka Boot - Mens 10.5 Black Boot Medium

Nunn Bush Circuit DC Plain Toe Chukka Boot - Mens 10.5 Black Boot Medium

*Casual boot from Nunn Bush *Mixed-material upper *Lace-up front closure *Breathable mesh linings *Fully cushioned Comfort Gel footbed *Two-toned outsole more

$84.95

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Nunn Bush Circuit DC Plain Toe Chukka Boot - Mens 8.5 Black Boot Medium

Nunn Bush Circuit DC Plain Toe Chukka Boot - Mens 8.5 Black Boot Medium

*Casual boot from Nunn Bush *Mixed-material upper *Lace-up front closure *Breathable mesh linings *Fully cushioned Comfort Gel footbed *Two-toned outsole more

$84.95

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Men's Men's Veymont Waterproof Hiking Boots by Propet in Black Red (Size 10.5 3E)

Men's Men's Veymont Waterproof Hiking Boots by Propet in Black Red (Size 10.5 3E)

Waterproof bootie construction inside a suede Nubuck and mesh upper with padded collar and tongue and abrasion resistant rubber toe cap.OrthoLite® X40™ sets the industry standard for high rebound performance with an elasticity rating over 40%.EVA... more

$164.99

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Men's Men's Veymont Waterproof Hiking Boots by Propet in Black Red (Size 10 5E)

Men's Men's Veymont Waterproof Hiking Boots by Propet in Black Red (Size 10 5E)

Waterproof bootie construction inside a suede Nubuck and mesh upper with padded collar and tongue and abrasion resistant rubber toe cap.OrthoLite® X40™ sets the industry standard for high rebound performance with an elasticity rating over 40%.EVA... more

$164.99

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Men's Men's Veymont Waterproof Hiking Boots by Propet in Gunsmoke Orange (Size 10 1/2 M)

Men's Men's Veymont Waterproof Hiking Boots by Propet in Gunsmoke Orange (Size 10 1/2 M)

Waterproof bootie construction inside a suede Nubuck and mesh upper with padded collar and tongue and abrasion resistant rubber toe cap.OrthoLite® X40™ sets the industry standard for high rebound performance with an elasticity rating over 40%.EVA... more

$164.99

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Muck Boots Fieldblazer 16" Hunting Boots Rubber Men's, Mossy Oak Country DNA SKU - 303688

Muck Boots Fieldblazer 16" Hunting Boots Rubber Men's, Mossy Oak Country DNA SKU - 303688

Get Comfortable. Get the Original. Fieldblazer Classic brings back the boot that started a revolution. Refreshed with a new lining package that acts as both a safety and comfort feature, the Classics stay with the same great last for the best in... more

$150.00

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Muck Boots Pathfinder 15" Rubber Boots Rubber Men's, Mossy Oak Country DNA SKU - 380486

Muck Boots Pathfinder 15" Rubber Boots Rubber Men's, Mossy Oak Country DNA SKU - 380486

Built for pursuit in most cold weather conditions, the Pathfinder finds itself at home in a variety of environments. 100% Waterproof and 100% MUCKPROOF, the 5mm neoprene bootie is designed for comfort, performance, and all day wear. Inspired by the... more

$165.00

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Muck Boots Fieldblazer 16" Hunting Boots Rubber Men's, Mossy Oak Country DNA SKU - 307701

Muck Boots Fieldblazer 16" Hunting Boots Rubber Men's, Mossy Oak Country DNA SKU - 307701

Get Comfortable. Get the Original. Fieldblazer Classic brings back the boot that started a revolution. Refreshed with a new lining package that acts as both a safety and comfort feature, the Classics stay with the same great last for the best in... more

$150.00

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Rugged Bucks Chukka Boot

Rugged Bucks Chukka Boot

Men's Rockport Rugged Bucks Chukka Boot - Brown - Casual boots Venture out in the wilderness with utmost comfort in the Rockport Rugged Bucks chukka boot. A flexible and outdoor-friendly design, this boot showcases Hydro-Shield construction that... more

$99.99

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Theo Chukka Boot

Theo Chukka Boot

Men's Thomas & Vine Theo Chukka Boot - Black - Casual boots The Theo chukka boot from Thomas & Vine is a happy medium between casual and formal. Boasting a low-cut profile, this boot showcases 12mm Tru Comfort Foam insole that delivers cushioned... more

$49.99

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

FREE shipping

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass... more

$141.50

FREE shipping

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank and... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10 Wide DDB0248-10-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10 Wide DDB0248-10-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10 Wide DDB0248-10-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank and... more

$141.50

FREE shipping

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

FREE shipping

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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

$141.50

FREE shipping

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Vance Co. Shoes Barett Knit Chukka Boot - Black - 9

Vance Co. Shoes Barett Knit Chukka Boot - Black - 9

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Grey - 11.5

Vance Co. Shoes Barett Knit Chukka Boot - Grey - 11.5

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Black - 10

Vance Co. Shoes Barett Knit Chukka Boot - Black - 10

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Black - 13

Vance Co. Shoes Barett Knit Chukka Boot - Black - 13

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Blue - 10

Vance Co. Shoes Barett Knit Chukka Boot - Blue - 10

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Blue - 11

Vance Co. Shoes Barett Knit Chukka Boot - Blue - 11

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Grey - 10

Vance Co. Shoes Barett Knit Chukka Boot - Grey - 10

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Grey - 8.5

Vance Co. Shoes Barett Knit Chukka Boot - Grey - 8.5

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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Vance Co. Shoes Barett Knit Chukka Boot - Grey - 8

Vance Co. Shoes Barett Knit Chukka Boot - Grey - 8

The Barett boots from Vance Co. will have you walking around in all the comfort you want with their 12 mm Tru Comfort Foamâ„¢ insole and mesh fabric uppers. Their cushioned collar and lightweight outsole will take this boot from old to bold, giving you... more

$74.99

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